TWI504605B - Magnesium bis( dialkyl amide) compound and method of producing magnesium-containing thin film using same - Google Patents

Description

Bis(dialkylguanidino) magnesium compound and method for producing magnesium-containing film using the same

The present invention relates to a novel bis(dialkylguanidino) magnesium compound, and a method for producing a magnesium-containing film by chemical vapor deposition (Chemical Vapor Deposition method; hereinafter referred to as CVD method) using the magnesium compound .

Heretofore, as a magnesium compound for producing a magnesium-containing film, for example, various kinds of magnesium compounds such as alkyl magnesium, magnesium alkoxide, and magnesium diketonate have been studied (for example, refer to Patent Documents 1 and 2). Among them, bis(cyclopentadienyl)magnesium or a related compound thereof is mainly used as a compound.

On the other hand, as a raw material for forming a metal-containing thin film such as a titanium-containing thin film, a zirconium-containing thin film, a niobium-containing thin film, or an aluminum-containing thin film, a compound having a dialkyl guanamine-based ligand is proposed (refer to the patent literature). 3).

In addition, a bis(dialkylguanidinium) magnesium compound is also known, and is used as a raw material for production of, for example, a catalyst for polymerization, a pharmaceutical, or a pesticide (for example, refer to Non-Patent Document 1 and Patent Document 4) ).

[Practical Technical Literature]

[Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2002-170993

[Patent Document 2] Japanese Patent Laid-Open Publication No. 2005-298874

[Patent Document 3] Japanese Patent Laid-Open Publication No. 2007-153869

[Patent Document 4] European Patent Application No. 1031581

[Non-patent literature]

[Non-Patent Document 1] J. Org. Chem., Vol. 43, No. 8, pp. 1564-1566 (1978)

However, in the manufacture of magnesium-containing films, conventional magnesium compounds are not necessarily most suitable for vapor pressure, thermal stability, reactivity, etc., even the most commonly used bis(cyclopentadienyl) magnesium. It cannot be said to be a sufficient magnesium compound for producing a magnesium-containing film. Therefore, magnesium compounds which satisfy both physical properties such as vapor pressure, thermal stability, and reactivity have been sought.

That is, the object of the present invention is to solve the above problems, and to provide a magnesium compound which can be industrially applied to a magnesium-containing film by a simple method, and more specifically, to a CVD method. To make a film containing magnesium. Further, an object of the present invention is to provide a method for producing a magnesium-containing film using the magnesium compound.

The present invention relates to the following matters.

A bis(dialkylguanamine) magnesium compound represented by the formula (1)

(wherein R ¹ represents an isopropyl group or a branched alkyl group having 4 to 6 carbon atoms; and R ² represents a linear or branched alkyl group having 1 to 5 carbon atoms. However, R ^{1 is} excluded. And R ² is an isopropyl group, R ¹ and R ² are all isobutyl groups, and R ¹ is an isopropyl group and R ² is a methyl group.

A process for producing a bis(dialkylguanamine) magnesium compound which is a bis(dialkylguanidino) magnesium represented by the above formula (1) A compound, the production method characterized by comprising the step of: forming a dialkyl magnesium compound represented by the general formula (2)

(In the formula, R ³ and R ⁴ may be the same or different, and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms.)

Step of reacting with a dialkylamine represented by the general formula (3)

(wherein R ¹ represents an isopropyl group or a branched alkyl group having 4 to 6 carbon atoms; and R ² represents a linear or branched alkyl group having 1 to 5 carbon atoms. However, R ^{1 is} excluded. And R ² is an isopropyl group, R ¹ and R ² are all isobutyl groups, and R ¹ is an isopropyl group and R ² is a methyl group.

A process for producing a bis(dialkylguanamine) magnesium compound which is a bis(dialkylguanidino) magnesium represented by the above formula (1) A compound, the production method characterized by comprising the step of: making a dialkylamine represented by the formula (3)

(wherein R ¹ represents an isopropyl group or a branched alkyl group having 4 to 6 carbon atoms; and R ² represents a linear or branched alkyl group having 1 to 5 carbon atoms. However, R ^{1 is} excluded. And when R ² is an isopropyl group, when both R ¹ and R ² are isobutyl groups, and when R ¹ is an isopropyl group and R ² is a methyl group.)

a step of reacting with an alkyllithium to synthesize a dialkylguanidinyllithium compound represented by the formula (4);

(wherein R ¹ and R ² are synonymous with the above.)

a step of reacting a dialkyl guanamine lithium compound represented by the above formula (4) with a magnesium dihalide represented by the formula (5)

MgX ₂ (5)

(wherein, X represents a halogen atom.).

A method for producing a magnesium-containing film, which comprises using a bis(dialkylguanidinium) magnesium compound represented by the above formula (1) as a magnesium supply source for a magnesium-containing film by chemical vapor deposition Production method.

A raw material for forming a magnesium-containing thin film, comprising a bis(dialkylguanidino) magnesium compound represented by the above formula (1).

By the present invention, a novel bis(dialkylguanidino) magnesium compound which is particularly suitable for film formation by a CVD method can be provided. With this magnesium compound, a magnesium-containing thin film can be produced by a CVD method with good film forming properties.

The bis(dialkylguanidino)magnesium compound of the present invention is represented by the above formula (1).

In the above formula (1), R ¹ represents a branched alkyl group having 4 to 6 carbon atoms such as an isopropyl group, a tertiary butyl group, a tertiary pentyl group or a neopentyl group, and R ² represents a methyl group. A linear or branched alkyl group having 1 to 5 carbon atoms such as an ethyl group, an isopropyl group, a tertiary butyl group, a tertiary pentyl group or a neopentyl group. However, the case where both R ¹ and R ² are an isopropyl group, the case where both R ¹ and R ² are isobutyl groups, and the case where R ¹ is an isopropyl group and R ² is a methyl group are excluded.

Two R ¹ may be different, and two R ² may be different. However, since two compounds having the same R ^{1 and the} same two R ² are relatively easy to synthesize, it is preferred.

In a preferred embodiment of the present invention, R ¹ is a branched alkyl group having 4 to 5 carbon atoms, and R ² is a linear or branched alkyl group having 1 to 5 carbon atoms. R ^{1 is} particularly preferably a tertiary butyl group, a tertiary pentyl group or a neopentyl group. R ^{2 is} particularly preferably a methyl group, an ethyl group, an isopropyl group, a tertiary butyl group, a tertiary pentyl group or a neopentyl group. Further, R ^{1 is} preferably a tertiary butyl group or a tertiary pentyl group, more preferably a tertiary butyl group; and R ^{2 is} preferably a linear or branched alkyl group having 1 to 5 carbon atoms, more preferably Methyl, ethyl, isopropyl, tert-butyl, tertiary pentyl, neopentyl.

The bis(dialkylguanamine) magnesium compound of the present invention may, for example, be a compound represented by the following formulas (6) to (20).

The synthesis of the bis(dialkylguanidino)magnesium compound of the present invention can be carried out by the method represented by the following (A) or (B) (hereinafter also referred to as the reaction of the present invention).

(wherein R ¹ and R ² are synonymous with the above, and R ³ and R ⁴ represent a linear or branched alkyl group having 1 to 10 carbon atoms. Further, R ³ and R ⁴ may be the same or different. Also, X represents a halogen atom.)

[method (A)]

Process (A) is a process for reacting a dialkylmagnesium compound with a dialkylamine to synthesize a bis(dialkylguanidino)magnesium compound.

The dialkylmagnesium compound used in the reaction (A) of the present invention is represented by the above formula (2). In the formula (2), R ³ and R ⁴ represent a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tertiary butyl group, a n-pentyl group or a tertiary pentyl group. A linear or branched alkyl group having 1 to 10 carbon atoms such as a neopentyl group or a fluorenyl group. Further, R ³ and R ⁴ may be the same or different.

The dialkylmagnesium compound used in the reaction (A) of the present invention can be used as a commercially available product, and can be produced from magnesium metal by a known method. In the reaction (A) of the present invention, di(n-butyl)magnesium or n-butylethylmagnesium or the like is suitably used.

The dialkylamine used in the reaction (A) of the present invention is represented by the above formula (3). In the general formula (3), R ¹ and R ² correspond to the formula (1) of R ¹ and R ^2, with the same meaning as those described above.

Therefore, as the dialkylamine used in the reaction (A) of the present invention, a tertiary butylmethylamine, a tertiary butylethylamine, a tertiary butyl isopropylamine, a di-tertiary butyl group is preferred. Amine, tertiary butyl tertiary pentylamine, di- or tertiary amylamine.

The dialkylamine is used in an amount of preferably 1.5 to 3.0 moles, more preferably 1.8 to 2.2 moles, per mole of the magnesium dialkylmagnesium.

The reaction (A) of the present invention is preferably carried out in an organic solvent. The organic solvent to be used is not particularly limited as long as it does not inhibit the reaction, and examples thereof include ethers such as diethyl ether, tetrahydrofuran, dimethoxyethane, and dioxane; An aliphatic hydrocarbon such as hexane, heptane, cyclohexane, methylcyclohexane or ethylcyclohexane; an aromatic hydrocarbon such as toluene or xylene; preferably an ether or an aliphatic hydrocarbon or A mixed solvent of an ether and an aliphatic hydrocarbon. Further, these organic solvents may be used singly or in combination of two or more.

The amount of the organic solvent used is preferably 1 to 100 g, more preferably 1 to 10 g, per 1 g of the dialkylmagnesium.

The reaction (A) of the present invention is carried out, for example, by a method in which a dialkylmagnesium compound, a dialkylamine, and an organic solvent are mixed and stirred, and reacted. The reaction temperature at the time of the reaction is preferably -20 to 120 ° C, more preferably 0 to 100 ° C, and the reaction pressure is not particularly limited.

[method (B)]

The method (B) is a method of reacting a dialkyl guanamine lithium synthesized from a dialkylamine with an alkyllithium with a magnesium dihalide to synthesize a bis(dialkylguanidino)magnesium compound.

The dialkylamine used in the reaction (B) of the present invention is represented by the above formula (3). In the general formula (3), R ¹ and R ² correspond to the formula (1) of R ¹ and R ^2, with the same meaning as those described above.

The alkyllithium used in the reaction (B) of the present invention is not particularly limited, and examples thereof include methyllithium, ethyllithium, n-butyllithium, secondary butyllithium, and tertiary butyllithium. However, it is preferred to use n-butyllithium.

The alkyl lithium is used in an amount of preferably from 0.8 to 1.2 mol, more preferably from 0.9 to 1.1 mol, based on 1 mol of the dialkylamine.

In the reaction (B) of the present invention, a dialkyl guanamine lithium is synthesized from a dialkylamine and an alkyllithium, and the dialkylguanidinium lithium is reacted with a magnesium dihalide.

The magnesium dihalide used in the reaction (B) of the present invention is represented by the above formula (5). In the above formula (5), X represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and is preferably a chlorine atom.

The amount of the above-mentioned magnesium dihalide used is preferably from 0.3 to 0.6 mol, more preferably from 0.45 to 0.55 mol, based on 1 mol of the dialkylamine. In the case where the dialkyl guanidinyl lithium is isolated, the amount of the dialkyl guanidinyl lithium used is 1 mol with respect to the magnesium dihalide, preferably 1.5 to 3.0 mol, more preferably 1.8 to 2.2. Moor.

The reaction (B) of the present invention is preferably carried out in an organic solvent. The organic solvent to be used is not particularly limited as long as it does not inhibit the reaction, and examples thereof include ethers such as diethyl ether, tetrahydrofuran, dimethoxyethane, and dioxane; An aliphatic hydrocarbon such as hexane, heptane, cyclohexane, methylcyclohexane or ethylcyclohexane; an aromatic hydrocarbon such as toluene or xylene; preferably an ether or an aliphatic hydrocarbon or A mixed solvent of an ether and an aliphatic hydrocarbon. Further, these organic solvents may be used singly or in combination of two or more.

The amount of the organic solvent used is preferably 1 to 100 g, more preferably 1 to 10 g, per 1 g of the dialkylamine. In the case where the dialkyl guanamine lithium is isolated, the amount of the organic solvent used in the reaction of the lithium dialkyl guanamine lithium with the magnesium dihalide is 1 g, preferably 1 to 100 g, based on 1 g of the magnesium dihalide. More preferably 1~10g.

The reaction (B) of the present invention is carried out, for example, by the following method. In other words, a dialkylamine, an alkyllithium, and an organic solvent are mixed and stirred to react to synthesize a dialkyl guanamine lithium compound, followed by addition of a magnesium dihalide, and then reacted while stirring; Alternatively, the synthesized dialkyl guanidinium lithium may be isolated, and then the obtained dialkyl guanidinium lithium, magnesium dihalide, and an organic solvent may be mixed and stirred for reaction. The reaction temperature at the time of the reaction is preferably -20 to 100 ° C, more preferably 0 to 50 ° C, and the reaction pressure is not particularly limited. Further, before the dialkyl guanamine lithium compound is reacted with the magnesium dihalide, the reaction liquid may be used as it is, or may be used as it is, or may be appropriately changed, removed, and/or Add organic solvent.

The bis(dialkylguanidinyl)magnesium compound of the object can be obtained by the reaction (A) or (B) of the present invention. After the completion of the reaction, the synthesized bis(dialkylguanidino) magnesium compound is isolated and purified by a known method such as extraction, filtration, concentration, distillation, sublimation, recrystallization, column chromatography, and the like.

Further, since the bis(dialkylguanamine) magnesium compound of the object of the present invention and the dialkylmagnesium used in the production thereof are unstable to moisture or oxygen in the atmosphere, it is preferably in the anhydrous condition. The reaction operation or the post treatment of the reaction liquid or the like is carried out under inert gas conditions.

With the bis(dialkylguanidinium) magnesium compound of the present invention, a magnesium-containing thin film can be formed with good film forming properties by, for example, a CVD method.

The method of depositing a magnesium-containing thin film on a film formation object can be carried out by a well-known CVD method or an atomic layer deposition method (ALD method), for example, by using bis(dioxane) under normal pressure or reduced pressure. a hydrazine-based magnesium compound vapor and an oxygen source (for example, an oxidizing gas such as oxygen or ozone; water; an alcohol such as methanol, ethanol, n-propanol, isopropanol or n-butanol) or a reducing gas (for example, Hydrogen or ammonia gas or a mixed gas of such gases is fed together to the heated film formation object to deposit a magnesium-containing film. Further, the gases (including the vaporized liquid) may be diluted by an inert gas or the like. Further, the magnesium-containing thin film may be deposited by a plasma CVD method by supplying the same raw material.

In the CVD method, a bis(dialkylguanidino)magnesium compound must be vaporized in order to form a film, however, as a method of vaporizing a bis(dialkylguanidino)magnesium compound used in the present invention, for example, In addition to the method of filling or transporting the bis(dialkylguanidinium) magnesium compound itself into a gasification chamber to be vaporized, it may be diluted with a suitable solvent using a pump for liquid transportation (for example, An aliphatic hydrocarbon such as an alkane, cyclohexane, methylcyclohexane, ethylcyclohexane, heptane or octane; an aromatic hydrocarbon such as toluene, ethylbenzene or xylene; ethylene glycol dimethyl ether; A solution of a bis(dialkylguanidinium) magnesium compound in an ether such as ethylene glycol dimethyl ether, triethylene glycol dimethyl ether, dioxane or tetrahydrofuran, etc., is introduced into a gasification chamber to be gasified Method (solution method).

In the case of depositing a magnesium-containing thin film by using the bis(dialkylguanidino) magnesium compound of the present invention, as the deposition condition, for example, the pressure in the reaction system is preferably from 1 Pa to 200 kPa, more preferably from 10 Pa to 110 kPa; The temperature of the film formation object is preferably from 50 to 900 ° C, more preferably from 100 to 600 ° C; and the temperature at which the bis(dialkyl guanamine) magnesium compound is vaporized is preferably from 30 to 250 ° C, more preferably 60. ~200 °C.

Further, as a source of oxygen (for example, an oxidizing gas, a water vapor or an alcohol vapor, or a mixed gas of such gases) or a reducing gas (for example, hydrogen or ammonia gas) with respect to the total gas amount at the time of depositing the magnesium-containing film, The content ratio of the mixed gas of the gases is preferably from 3 to 99% by volume, more preferably from 5 to 98% by volume.

[Examples]

Next, the present invention will be specifically described by way of examples, but the scope of the invention is not limited to the examples.

Example 1 (Method (A); Synthesis of bis(tertiary butylmethylguanidino) magnesium (compound (6)))

After adding 5.5 g (0.23 mol) of metallic magnesium and 20 ml of diethyl ether to a flask containing 100 ml of a stirring apparatus, a thermometer, and a dropping funnel in an argon atmosphere, 3.0 g (21 mmol) of bromobutane was slowly added. Drop it. Next, 180 ml of diethyl ether and 25 g (0.18 mol) of bromobutane were slowly dropped, and the mixture was reacted at 40 ° C for 2 hours while stirring, and then 55 g (0.62 mol) of dioxane was added thereto while stirring. The reaction was allowed to proceed for 2 hours at °C. After the completion of the reaction, the reaction mixture was filtered under argon, and the filtrate was concentrated under reduced pressure. The concentrate was vacuum dried while heating to obtain 22 g of dibutylmagnesium (isolation yield; 80%).

Next, 7.0 g (50 mmol) of the previously obtained dibutylmagnesium and 70 ml of heptane were added to a flask having a 200 ml inner volume of a stirring device, a thermometer, and a dropping funnel in an argon atmosphere, and the liquid temperature was maintained at 25°C. In the vicinity of °C, 10 g (0.11 mol) of tributylmethylamine was slowly dropped, and the mixture was reacted at 25 ° C for 3 hours while stirring. After the completion of the reaction, the reaction mixture was concentrated, and then subjected to sublimation under reduced pressure (140 ° C, 20 Pa) to give 6.4 g of bis(tris-butylmethyl phthalamide) magnesium as a white solid (isolation yield; 66%) ).

Further, bis(tertiary butylmethylguanidino) magnesium is a novel compound exhibiting the following physical property values.

¹ H-NMR (tetrahydrofuran-d ₈ , δ (ppm)); 2.58 (3H, s), 1.03 (9H, s) melting point; 140 to 141 °C.

Example 2 (Method (A); Synthesis of bis(tertiary butylethylguanidinium) magnesium (compound (7))

The reaction was carried out in the same manner as in Example 1 except that the dialkylamine in Example 1 was changed to 11 g (0.11 mol) of tributylethylamine. As a result, 5.8 g of bis(tertiary butylethylguanidino)magnesium as a white solid was obtained (yield: 52%).

Further, bis(tertiary butylethylguanidino) magnesium is a novel compound exhibiting the following physical properties.

¹ H-NMR (tetrahydrofuran-d ₈ , δ (ppm)); 2.90 (2H, q, 6.8 Hz), 1.07 (9H, s), 0.97 (3H, t, 6.8 Hz)

Melting point; 75~78°C

Example 3 (Method (B); Synthesis of bis(tertiary butyl isopropyl guanyl) magnesium (compound (8))

In a argon atmosphere, 1.8 g (16 mmol) of tributyl isopropylamine and 30 ml of heptane were placed in a flask equipped with a stirring apparatus, a thermometer, and a dropping funnel. Then, while maintaining the liquid temperature at around 25 ° C, 10 ml (16 mmol) of a 1.6 mol/l n-butyllithium/hexane solution was slowly dropped, and the mixture was reacted at 25 ° C for 2 hours while stirring. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure to give 1.7 g of butyl isopropyl phthalamide (yield: 88%).

Next, 0.40 g (4.2 mmol) of magnesium chloride and 10 ml of tetrahydrofuran were placed in a flask equipped with a stirring apparatus, a thermometer, and a dropping funnel of 50 ml. Then, while maintaining the liquid temperature at around 25 ° C, 10 ml of a tetrahydrofuran solution of 1.0 g (8.3 mmol) of tertiary butyl isopropyl guanamine lithium was slowly dropped, and the mixture was reacted at 25 ° C for 8 hours while stirring. After the completion of the reaction, the reaction solution was concentrated under reduced pressure, and then 20 ml of hexane was added to the concentrate, and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the concentrate was distilled under reduced pressure (120 ° C, 5.7 Pa) to give a pale yellow liquid of bis(tris-butyl isopropyl phthalamide) magnesium 0.53 g (single From yield; 50%).

Further, bis(tertiarybutylisopropylammonium)magnesium is a novel compound exhibiting the following physical property values.

¹ H-NMR (tetrahydrofuran-d ₈ , δ (ppm)); 2.99 (1H, sept, 6.6 Hz), 1.14 (9H, s), 0.99 (6H, d, 6.6 Hz)

Example 4 (Method (B); Synthesis of bis(tertiary butyl tertiary pentylguanidino) magnesium (compound (10))

In a argon atmosphere, 1.1 g (8.0 mmol) of tributyl butyl tertiary amine and 15 ml of heptane were added to a flask containing a stirring apparatus, a thermometer, and a dropping funnel in an internal volume of 100 ml, while maintaining the liquid temperature. In the vicinity of 25 ° C, 5.0 ml (8.0 mmol) of a 1.6 mol/l n-butyllithium/hexane solution was slowly dropped, and the mixture was reacted at 25 ° C for 2 hours while stirring. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure to give <RTI ID=0.0>>

Next, 0.16 g (1.7 mmol) of magnesium chloride and 10 ml of tetrahydrofuran were added to a flask equipped with a stirring apparatus, a thermometer, and a dropping funnel of 50 ml, and the tertiary butyl group was slowly dropped while maintaining the liquid temperature at around 25 °C. 10 ml of a solution of 0.51 g (3.4 mmol) of a tertiary pentylguanidinyllithium in tetrahydrofuran was allowed to react at 25 ° C for 8 hours while stirring. After the completion of the reaction, the reaction solution was concentrated, and then 20 ml of hexane was added, and the mixture was stirred and filtered. The filtrate was concentrated under reduced pressure to give 0.31 g (yield: 60%) of bis(tris-butyl-tert-yt-ytylamino) magnesium as a pale yellow solid.

Further, bis(tertiary butyl tertiary pentylguanidino) magnesium is a novel compound exhibiting the following physical properties.

¹ H-NMR (tetrahydrofuran-d ₈ , δ (ppm)); 1.44 (4H, q, 7.3 Hz), 1.20 (18H, s), 1.12 (12H, s), 0.85 (6H, t, 7.3 Hz)

Melting point; above 170 ° C

Example 5 (deposition experiment; manufacture of magnesium-containing film)

Using the bis(tertiary butylmethylguanamine) magnesium (compound (6)) obtained in Example 1, a deposition experiment by a CVD method was carried out, and the properties of the film formation were evaluated. In the deposition experiment, the apparatus shown in Fig. 1 was used. The deposition conditions and the characteristics of the film are as follows.

(deposition conditions)

Magnesium raw material; bis(tertiary butylmethyl guanamine) magnesium (compound (6))

Gasification temperature; 100 ° C

He carrier flow; 100sccm

Oxygen flow rate; 10sccm

Substrate material; SiO ₂ /Si

Substrate temperature; 300 ° C

Pressure in the reaction system; 1.33 kPa

Deposition time; 30 minutes

(Characteristics of the film (XPS-depth))

Film thickness; 50nm or more

XPS analysis; magnesium oxide film

Carbon content; not detected

Nitrogen rate; not detected

The device shown in Figure 1 has the configuration described below. In the magnesium raw material container (gasifier) 7 held at a constant temperature by the constant temperature bath 8, the magnesium compound is heated and vaporized, and is discharged from the raw material container 7 together with the helium gas introduced through the mass flow controller 4. . The gas discharged from the raw material container 7 is introduced into the reactor 9 together with the helium gas introduced through the mass flow controller 5. On the other hand, the oxygen of the reaction gas is also introduced into the reactor 9 via the mass flow controller 6. The pressure in the reaction system is monitored by a pressure gauge 12, and the pressure in the reaction system is controlled to a predetermined pressure by a switch of a valve before the vacuum pump 14. The central portion of the reactor 9 has a configuration that can be heated by the heater 11. The magnesium compound introduced into the reactor 9 is positioned in the central portion of the reactor, and is thermally decomposed on the surface of the substrate 10 heated to a predetermined temperature by the heater 11, and a magnesium-containing thin film is formed on the substrate 10. The gas discharged from the reactor 9 is discharged to the atmosphere via a trap 13 and a vacuum pump 14.

Comparative Example 1 (deposition experiment; manufacture of magnesium-containing film)

A deposition experiment by a CVD method was carried out in the same manner as in Example 5 using bis(cyclopentadienyl)magnesium, and the properties of the film formation were evaluated. The deposition conditions and the characteristics of the film are as follows. Further, various conditions were adjusted so that the supply amount of the raw material was in accordance with Example 5, and a deposition experiment was carried out.

(deposition conditions)

Magnesium raw material; bis(cyclopentadienyl)magnesium

Gasification temperature; 30 ° C

He carrier flow; 10sccm

Diluted He flow; 90sccm

Oxygen flow rate; 10sccm

Substrate material; SiO ₂ /Si

Substrate temperature; 300 ° C

Pressure in the reaction system; 10 Torr (about 1.33 kPa)

Deposition time; 30 minutes

(The characteristics of the film (XPS depth measurement))

Film thickness; 50nm or more

XPS analysis; magnesium oxide film

Carbon content; 30% (converted by carbon atom)

Nitrogen content; not detected (originally no nitrogen atom in the raw material)

From the above results, it was confirmed that a high-quality magnesium-containing film (magnesium oxide film) containing no impurities such as carbon atoms or nitrogen atoms can be produced by using the bis(dialkylguanidinium) magnesium compound of the present invention.

[Industrial use possibility]

According to the present invention, it is possible to provide an industrially applicable novel magnesium compound capable of producing a magnesium-containing film by a simple method, and more particularly, to provide a magnesium compound suitable for producing a magnesium-containing film by a CVD method. Moreover, the magnesium compound can provide a method of producing a magnesium-containing thin film on a film formation object by a CVD method. The bis(dialkylguanidinium) magnesium compound is, for example, a useful compound as a raw material for producing a magnesium-containing thin film, a catalyst for polymerization, a pharmaceutical, or a pesticide.

1. . . Carrier gas (He)

2. . . Dilution gas (He)

3. . . Reaction gas (O ₂ )

4. . . Mass flow controller

5. . . Mass flow controller

6. . . Mass flow controller

7. . . Magnesium raw material container (gasifier)

8. . . Thermostat

9. . . reactor

10. . . Substrate

11. . . Reactor heater

12. . . pressure gauge

13. . . collector

14. . . Vacuum pump

BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a view showing the construction of a deposition apparatus for producing a magnesium-containing film using a bis(dialkylguanidino) magnesium compound used in the examples.

1. . . Carrier gas (He)

2. . . Dilution gas (He)

3. . . Reaction gas (O ₂ )

4. . . Mass flow controller

5. . . Mass flow controller

6. . . Mass flow controller

7. . . Magnesium raw material container (gasifier)

8. . . Thermostat

9. . . reactor

10. . . Substrate

11. . . Reactor heater

12. . . pressure gauge

13. . . collector

14. . . Vacuum pump

Claims (4)

a bis(dialkylguanamine) magnesium compound represented by the formula (1) In the formula, R ¹ represents a third butyl group, and R ² represents a methyl group or an ethyl group. A process for producing a bis(dialkylguanidino)magnesium compound which is a bis(dialkyl group) represented by the formula (1) as in the first aspect of the patent application a mercapto) magnesium compound, which is characterized by comprising the steps of reacting a dialkylmagnesium compound represented by the formula (2) with a dialkylamine represented by the formula (3); In the formula, R ³ and R ⁴ may be the same or different, and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms; Wherein R ¹ represents a third butyl group, and R ² represents a methyl group or an ethyl group; In the formula, R ¹ and R ² are synonymous with the above. A method for producing a magnesium-containing film, which is a method for producing a magnesium-containing film by chemical vapor deposition using a bis(dialkylguanidinium) magnesium compound as the magnesium supply source according to claim 1. A raw material for forming a magnesium-containing film comprising the bis(dialkylguanidino) magnesium compound as in the first aspect of the patent application.